The Perfect First Date
by iheartnywriter
Summary: My version of Serena and Dan's first date from Season 1. Maybe a one shot, maybe I'll continue if people like it : Please read and review! :
1. Chapter 1

**A/N Hi, thanks for reading my 2nd fan fiction. I just came up with this idea and I'm not sure if I'll continue it or if it will be a one shot. Please review so that I can know if people are even interested so that I can continue writing, I also love advice! I would love to talk to people about Gossip Girl too. I hope you like it :) **

**Chapter 1**

Dan checked the time again. He still had an hour before he could go pick up Serena for their first official date. He couldn't believe how lucky he was to have a shot with Serena van Der Woodsen.

"Hey Dan." Jenny, his little sister closed the loft's door behind her, her hands full with shopping bags.

"Hey. What have you been up to?"

"Just went to pick up some more fabric. I'm making some headbands for Blair and the other girls." She set the bags down in her room before popping a bagel in the toaster.

"Oh really? Well I hope they don't have you being their slave." She laughed, pulling out the cream cheese.

"Well, not that it's any of your business, but I do all these things because I want to." She started smearing cream cheese on the bagel, offering some to Dan.

"No thanks. I hope that's really the case."

"Enough about me, you have your date with Serena don't you?" She exclaimed, happy that her brother finally had a chance with his dream girl.

"Yeah, yeah I do. I'm actually pretty nervous, believe it or not." She smirked.

"You will be fine. After all, you can't be too bad if she agreed." She said, dodging a playful slap from Dan.

"Very funny. I actually have to go. See you later." He grabbed his phone and a blanket, heading out the door.

"Have fun!" Jenny cried, as he shut the door.

Dan headed out into the warm air. He took the metro to Manhattan, finally arriving at Serena's apartment. The receptionist rung him up and he stepped into the elevator with a man dressed in a suit.

"Nervous about something?" Said the guy. Dan hadn't noticed he was cracking his knuckles.

"First date." Said Dan, sheepishly.

"Ah, been there. Good luck." He said with a smile as he stepped off on his floor. The elevator dinged and Dan walked to Serena's door. Taking a deep breath, he rung the doorbell. Serena opened the door, wearing a blue maxi dress that matched her eyes perfectly.

"Hi!" She exclaimed, giving him a hug.

"Hey, how are you?" Dan said.

"Happy that your finally here." She smiled. She closed the door behind her and started walking alongside Dan.

"As am I." They took the elevator ride down, waving to the receptionist.

"My mom has been all over me about going back to normal at school and everything. I'm sick of it. She just can't understand that with Blair as a best friend, one fight can completely change everything at school." She vented. Dan thought for a minute before replying.

"Well, you could try to explain that to her maybe."

"Sure, I guess I could try." Serena was obviously annoyed with her mother.

"Okay, how about this. We forget all about our annoying family drama, and have a fun time?" Dan said, smiling wide.

"That sounds like a great idea!" She flashed her glistening smile at him, grabbing his hand as they kept walking along the sidewalk. Dan could feel his heartbeat rise.

"I know this great cafe right around this corner. I was thinking we could get some sandwiches and head to Central Park?" She nodded, they rounded the corner and coming across an adorable cafe, with flower pots and a patio.

"This is so cute!" Serena pulled him in the store. They decided on grilled cheese sandwiches and iced tea.

"How's Jenny doing, with trying to fit in and all?" Serena asked, taking a sip of her drink.

"She's fine, according to her. She keeps coming home with all these new projects she's doing for Blair though." Dan said, spotting Central Park in the distance.

"Huh. Well if Blair has anything to do with it, I'm sure Jenny's doing them for something."

"Yeah, maybe." Dan said. They crossed the street and sat down on the blanket Dan had brought.

"This is so nice!" Said Serena. They ate their sandwiches, talking about their lives.

"My mom left for the summer, to Hudson, supposedly to be an artist, but she hasn't come home and hasn't mentioned it. I'm positive she's left us for good, but my dad and Jenny don't see that."

"Oh Dan, I'm sorry. I hope you sort things out with her. I know what it's like to have a parent leave. My dad left when I was young, and never came back. He doesn't ever call or anything."

"I'm sorry to hear that. I hope I can work things out too. Hey, we weren't supposed to talk about family drama!" Serena laughed, sounding like a 4 year old, causing Dan to smile.

"Oh right!" They laughed some more, and finished up their sandwiches. The sun was bright, and they decided to lay down for a while. Eventually they both ended up falling asleep. After a couple of hours, Dan blinked his eyes open. He checked his watch, it was already 8.

"Serena." He whispered. She didn't stir.

"Hey, Serena." Dan shook her shoulder lightly. Her eyes opened.

"Oh, I fell asleep! I'm sorry." She said, embarrassed.

"So did I." He laughed.

"I guess it was hot and we just had lunch." She said leaning closer to him. She turned around on her front.

"Yeah. I guess so." He said. He leaned in closer to her, and their mouths met. She hadn't kissed someone like this in a long time. When they finally broke apart, smiling, Dan just said,

"Wow." She laughed. They turned to see the sun setting behind the trees, the sky a pink and orange color.

"Yeah, that's right. This has been the perfect first date."

"It sure has." They layed there for a while, taking about their hobbies and passions. Their accomplishments and goals. A while later, they picked up their things, threw the trash away, and walked hand in hand back to Serena's apartment.

"You know, I'll be honest with you. I never thought I'd get the chance to go out with you."

She blushed.

"Well, your the sweetest, most honest, and compassionate guy I have ever gone out with." Now it was his turn to blush. He leaned in to kiss her goodbye.

"Thanks for walking me home. And for this date, it's been the best time I've had in a while. See you on Monday!"

"It was my pleasure. See you!" She kissed his cheek, before turning to go into the hotel. Dan smiled as she waved before going back to elevators. He was smiling the entire way home...


	2. Chapter 2

**A/N Thanks for reviewing! That's why I've decided to keep writing some more on this fic, as long as people actualy like it :P Thanks for reading!**

**Chapter 2**

"Hey Dan, I was wondering if you wanted to go out again sometime soon? I'm free all week, so give me a call. Bye!" Serena left a message on Dan's cell phone. She wasn't the clingy type, but she couldn't help but call Dan again after their date last. He was the sweetest boy he'd been out with in a long time. Nothing compared to all the rude, desperate guys from boarding school.

"Hey, what are you up to?" Eric asked, as he grabs some juice from the fridge.

"Oh nothing. You?" She puts her phone back in her pocket and takes a seat beside Eric.

"I was going to go out with some friends, but I could stay in if you like, and we could do something?" Serena shakes her head.

"No, you go and have fun! Besides, I've got to buy some new boots." She smiles encouragingly at him.

"Allright. Have you seen Mom today?" Just then, Serena's phone rings.

"Sorry." She answers. "Hello."

"Hey Serena, I just got your message." Dan says on the other line.

"Hi! How are you?"

"Pretty good, you?"

"I'm great." She replys.

"Good. So about that date, are you free today?" He crosses his fingers.

"Yeah, I am." She smiles.

"Great, cause I'm probably the only guy who isn't going to a party on a Saturday night." Serena laughs at his remark.

"Well, I'll be right there beside you. Do you want to go see a movie?"

"Sounds great. I'll pick you up at 6." They hung up and Serena ran to her closet, already preparing something to wear.

That night, Dan and Serena were in a taxi on the way home from their date. Suddenly, Dan's phone rings.

"Hey Dan, where are you?" Jenny said on the other line. He could hear her sniffling.

"Hi, is everything okay? I'm in a taxi, heading home."

"Okay. Yes, everythings fine. I just wanted to talk, but if your busy I'll just see you at home."

"Alright, if your sure." He hung up.

"That was Jenny, she sounded upset." Dan said, confused.

"Well maybe something to do with school?" Serena suggested.

"Yeah, I'll talk to her when I get home."

"So today was fun. I wasn't expecting to do anything today." She smiles.

"Me either. I really like spending timw with you."

"Oh yeah?" She leans in close to him and kisses him.

"Definitley." He says, kising her again.

They finally pull up in front of Serena's apartment.

"Could you wait here a minute please?" Dan tells the driver. He nods. Dan opens his door, jogging to the other side to open it for Serena. He grabs her hand and they walk to the door.

"Thanks for tonight. I'll see you at school Monday okay?"

"For sure. Goodnight." He gives her one last kiss and gets back to the taxi.


	3. Chapter 3

**A/N Thanks for reading!**

**Chapter 3**

Dan closed the loft door.

"Jenny?" He asks.

"Hey, where were you?" Dan can tell she's been crying.

"I was out with Serena. What's wrong?" He goes over to her and they take a seat on the couch.

"It's nothing."

"Jen, you can talk to me." He puts his hand on her shoulder.

"Well, today Blair told me that I'm not invited to the masquerade ball. Even though I always do everything she asks, apparently I'm not good enough." A tear rolls down her cheek.

"Oh Jenny, Blair is the most popular girl at school. Of course she's gonna try to make everyones lives difficult, she'll boss everyone around, but in the end, you'll find your real friends." Dan gives her a reassuring look and gives her a hug.

"Thanks Dan."

"Besides, we can do way better things than hide behind a mask all night." She giggles, nodding, and gets up to get some juice.

"Like what?" Dan looks trapped.

"Uhm." He quickly thinks of something. "Maybe you, me and Serena could all hang out. I know how much you like her right?"

"That would be so cool! Thanks Dan." She runs into her room. Dan hopes Serena will think so too.

Serena was brushing her hair the next morning, thinking about their time at the movies.

"_Where do you want to sit?" Asked Dan. Serena grabbed his hand, and pulled him to the back of the theatre._

"_Last row. If that's okay with you." She smiled. They sat down, just as the movie was starting. The movie they wanted to see had been sold out, so they were stuck watching a random documentary about birds. They sat down and Serena pulled Dan into a kiss._

"_This is perfect." Dan says._

"Serena!" Lily van Der Woodsen calls her daughter from the other room.

"Yeah?" Serena says as she walks to her mother's room.

"Have you seen Eric today? I wanted to talk to him about maybe going out for dinner tonight? Your not busy are you?" She said, looking at the red blouse in her hands.

"No I don't have any plans tonight. I saw him earlier, he said he was going out with Jenny."

"Oh alright. I'll call him when I get back."

"Where are you going?" Asked Serena, twirling a lock of her blonde hair on her finger.

"Shopping. Would you like to come with me?" Lily put down the shirt.

"Sure." She goes back to her room to finish getting ready. Her phone rings, and she runs to pick it up.

"Hello?"

"Hey Serena. How are you?" It's Dan.

"Good, you? Did you talk with Jenny when you got home last night?"

"Yeah I did. She was just upset that she wasn't invited to the Masquerade Ball."

"Oh, well I would offer to talk to Blair, but she probably doesn't want me to go either." Serena said.

"Yeah. Well the thing is, I kinda promised her that all three of us could hang out sometime." Dan closed his eyes, hoping she wouldn't find it annoying.

"Oh really! That would be fun, Jenny is great." Serena said honestly.

"I'm glad to hear that, I was afraid you would find that annoying." Dan admitted on the other line.

"No, no. Maybe tomorrow after school? Since it's the ball as well." Serena suggested.

"Sure, sounds good. See you then." They hang up and Serena grabs her bag before going to the couch to wait for her mom.

The following day after school, Serena met Dan and Jenny in the courtyard.

"Hey." Dan said as Serena walked towards them, before giving her a kiss on the cheek.

"Hi!" She replied, smiling brightly.

Hi Jenny!" She gave Jenny a hug, and they start walking. "So what are our plans for today? I'm excited!" Serena says.

"Well Jenny found this small high school art festival that's going on this week in Central Park, would you be cool with going there?"

"That sounds awesome!" Serena replied.

"Great." Jenny said, trying to hide her excitement that she was hanging out with the most popular girl at school. They walked down to Central Park, the air cold, talking about their school day. Serena pulled her purple scarf tighter around her neck. Soon after, Serena and Jenny's phones rung. It was from Gossip Girl, and Dan of course didn't have his phone set up with Gossip Girl alerts.

"Ugh, I can't believe it." Jenny said, looking dissapointed.

"What?" Dan asked, trying to peek at Serena's screen.

"It's just typical Gossip Girl, she's talking about the masquerade ball." She turned to Jenny. "Don't worry about it Jenny. I mean I'd rather hang out with you guys than to go." Serena said, putting her arm around Jenny's shoulder.

"Okay, thanks." As they neared Central Park, the day was getting colder. Dan's nose and cheeks were red from the air, and Jenny and Serena were still freezing in their wool coats. They turned the corner onto 5th Avenue. They spotted booths and tents set up, with artwork on display and for sale. There were also two guys playing guitar and singing folky songs.

"This is so cool!" Serena squealed, pulling on Jenny and Dan's arms.

"Awesome!" Jenny exclaimed, eyeing a painting of a mannequin wearing an orange gown. "This is so good." She commented, standing in front of the booth.

"Thanks." A girl with bright orange hair in a ponytail replied. "I made it myself."

"Cool. I love fashion, the dress is gorgeous." Jenny said, smiling at the girl before walking to where Serena and Dan were.

"This is so cool Jenny. I'm glad we came! I love this one!" Serena laughed, holding a handmade, engraved stone. The stone read one of Dan's favorite quotes:

"_Always dream and shoot higher than you know you can do."_

"Excuse me, how much are these?" Dan asked the guy behind the table.

"Twenty five bucks." He replied, polishing a rock.

"We'll take it" Dan said, grabbing some bills from his wallet.

"Oh Dan, you don't have to!" Serena said, obviously thrilled that her boyfriend was buying her a cute gift.

"I know, but I want to." He said, grinning. He handed over the cash, and the guy put the stone in a little black box before handing it to Serena.

"Thank you." She said warmly.

"Thanks guys!" The guy waved, before going back to his current project.

"I love it Dan. Thank you." Serena said before kissing him on the lips. The trio continued to walk down, seeing all the other booths and art pieces. Dan commented on a guys clown outfit, casuing all of them to burst out laughing, and Jenny realized that this was much better than going to the ball.


	4. Chapter 4

**A/N Thanks for reading! I decided that this will be the last "mini" chapter, so I hope you liked it :D**

**Chapter 4**

Serena and Dan walked hand in hand in Central Park.

"Let's take a seat." Dan said, motioning towards the park bench.

"Sure." Serena said, placing her leather bag beside her.

"Serena, I want to tell you something." Dan said, turning towards her.

"Okay, is something wrong Dan?" Serena asked.

"No, no. The opposite actually." He toom a deep breath before starting. "I just want to tell you that these past couple of months have been amazing. We have so much fun together and I feel that we have a connection. I love that your not afraid to be who you are in front of anyone and everyone, and you have made me feel comftorable being myself too. So... I want to tell you, that I love you." He said, looking into her deep blue eyes.

"Oh Dan, I love you too. Thank you for saying that. Your the best guy I've ever been lucky enough to call mine. I love you." She said before giving him a passionate kiss. Dan grinned, happy at how things turned out.

"Now what should we do?" He asked.

"Let's go eat something. I'm starving!" She said, jumping up and pulling him along, before running ahead of him.

"Hey wait up!"

"You'll have to run." Serena said laughing.

"You better go faster than that if you don't want me to catch you." Dan said, speeding up to catch his true love.


End file.
